N[C:2]1C=CC=CC=1.Cl.N([O-])=O.[Na+].[Cl-].[C:14]1([N+:20]#[N:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[O:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]1=[O:28].[OH-:29].[Na+]>O>[C:14]1([N:20]2[C:27]([CH3:2])=[CH:26][C:25](=[O:29])[C:24]([C:23]([OH:22])=[O:28])=[N:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1In a separate flask; 9.08 g of aniline is mixed with 37.5 ml of concentrated hydrochloric acid and 47 ml of water. The resulting solution is maintained at about 5° to 10° and a solution of 7.13 g of sodium nitrite in 24 ml of water is added. The resulting solution of phenyldiazonium chloride is added dropwise to the stirred pyrone solution, while maintaining a temperature of about 5° to 10°. The pH is maintained at about 8 to 9 by the addition of small amounts of sodium hydroxide solution.
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